Why you should care

Given her job, Emily Castor spends far more time traveling by air than by car. A typical week in her well-trodden shoes consists of a ribbon-cutting ceremony in Denver and schmoozing with chamber of commerce members in Los Angeles — her work includes delivering speeches at tedious transportation conferences, dragooning local transit officials into giving her the time of day and vouching for her company as a “last-mile solution” to fix “big, intractable transportation problems.”

Her agenda is more that of government factotum than startup director, but that’s what happens when emerging technology tries to gobble its way into policy. A self-professed transportation wonk, the 33-year-old Castor is the first-ever transportation-policy chief at Lyft. Her job: corralling public-private partnerships to get Lyft into every city in America. Playing peacemaker in an era when ride-sharing startups like Lyft and Uber are rousing ire in urbanists who’d prefer a greater city alliance on buses or bikes, she allies with city officials, urban planners, transportation agencies and environmental organizations to try to integrate Lyft into existing transportation systems and iron out bureaucratic kinks. Castor is campaigning for the company’s very right to exist, seeking to ensure governments “don’t feel that this is an evolution that they’re not part of,” she says.

Regulators have to backtrack.

Saba Waheed, UCLA Labor Center

It all fits into a narrative that Lyft has pitched since it entered a neck-and-neck race with Uber: We’re the nice guys, not the purely sharky capitalists, the company insists, pointing to its better protections for drivers and mobility services for the handicapped. But it’s not easy to fight a behemoth. Lyft commands a sizeable share of the market — about 25 percent, according to Aswath Damodaran, a finance professor at NYU’s Stern School of Business. But there’s little question that Uber, with its 11-figure market capitalization, is the Goliath here. (Uber did not reply to requests for comment.)

But Lyft is one of many budding startups — Airbnb, Spotify, 23andMe — where technology and customer acquisitions are almost secondary to exactly what many startuppers loathe most: the government. Companies like Lyft rose to prominence faster than the slow-moving law could react, says Saba Waheed, research director at the UCLA Labor Center and an expert on sharing economy businesses: “Regulators have to backtrack.… We’re still far from a relationship of negotiation and compromise.” Over the years, the embattled sharing economy has dredged up questions of safety, privacy and labor, with some startups “wanting to impact transportation without wearing the full gear of it,” as Waheed puts it. Such was the case with Lyft and Uber in Austin, Texas, where the ride-sharing giants’ fleets were unceremoniously driven out last year after a yearlong battle.

As of 2013, 45 percent of Americans lack access to public transit, down from 50 percent in 2009, according to the American Society of Civil Engineers. Castor’s job is to pitch Lyft as a solution to this problem, rather than an exacerbation of access gaps. Under her, Lyft has launched partnerships in 16 cities, including Miami, Dallas, Denver, Seattle and Los Angeles. Some of the splashy stunts this year: In January, Lyft launched a Web-based booking for those who don’t own a smartphone or credit cards; in August, a concierge system with wheelchair-accessible vehicles for disabled passengers in Denver. They’ve teamed up with with Seattle’s Department of Transportation to offer rides for inebriated bargoers, distributing free ride credits in or around neighborhoods with active nightlife and popular bars, and vouchers that fund the first- and last-mile ride to public transit for suburbanites who live far from train stations. (Lyft declined to provide any figures on the number of users or how much these programs cost the company.)

In the beginning, Lyft asked forgiveness when entering a new market. Now, she says, the company uses a lighter touch.

As the second employee hired to work on the Lyft product, when the startup was still a piddling experiment inside ride-share program Zimride, Castor has been on the front lines for the past four years. “Director of Transportation Policy” is her fourth title, after director of community relations, director of community engagement, and community manager. And just as she’s gone through many incarnations at Lyft, so too has the company’s approach to transportation policy: In the beginning, Lyft asked forgiveness when entering a new market. Now, the company uses a lighter touch, says Castor. And speaking of forgiveness — as part of the original team at Lyft, Castor has long been banned from using Uber, starting years before even those early Uber-Lyft smear campaigns that included ordering and canceling some 5,560 rides and poaching each other’s drivers.

As a former legislative aide for U.S. Congresswoman Susan Davis and a financial consultant for municipal infrastructure projects, Castor knows politics. “She’s a little bit preprogrammed,” says Art Guzzetti, vice president of policy at the American Public Transportation Association. And though, yes, she does sound a bit rehearsed, the script doesn’t hurt when you’re knee-deep in heated debates, he says. The wonkiness is complemented by a sunny beach vibe, a remnant of her college years at the University of California, San Diego. Meanwhile, Castor is “known at all levels of governance pretty widely across the U.S.,” says Susan Shaheen, co-director of the Transportation Sustainability Research Center at the University of California, Berkeley, who calls her “one of the most prolific, well-regarded speakers in shared mobility.”

Some say Castor’s olive-branch-waving is a facade. Don’t buy into “the PR” in which “Lyft plays the good cop” and “Uber plays the bad cop,” says Damodaran. For the most part, there’s little differentiation between the services, he says, and whether Uber or Lyft, the government has its hands tied and moves too sluggishly to catch up with them. Lyft, in turn, may not be able to catch Uber — which is valued at $68 billion to Lyft’s $5.5 billion — or the slew of other competitors, including Via, Grab and Google. Although Lyft is armed with $2 billion in funding, the company has yet to wrangle enough revenue to offset its spending. (Lyft is on a “path to profitability,” but would not share a timeline for when the company plans to break even — only the “promise of partnerships,” says Castor.)

As I exit the Lyft headquarters onto the clogged streets of San Francisco, I take out my phone to hail a ride. My Uber arrives within minutes.

An earlier version of this story stated that Lyft started within Zipcar, not Zimride; due to editing errors, we also mischaracterized aspects of Castor’s role and the timing of her ban from Uber.